# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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data_z
_database_code_depnum_ccdc_archive 'CCDC 910674'
#TrackingRef 'Z.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 N3 O5 S'
_chemical_formula_weight         521.62
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   13.8796(10)
_cell_length_b                   23.1960(17)
_cell_length_c                   8.6991(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.000(2)
_cell_angle_gamma                90.00
_cell_volume                     2785.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9341
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32345
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4920
_reflns_number_gt                3237
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1054P)^2^+5.3053P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4920
_refine_ls_number_parameters     334
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0865
_refine_ls_wR_factor_ref         0.2563
_refine_ls_wR_factor_gt          0.2238
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 3.45009(9) 0.87331(7) -1.44563(14) 0.0605(4) Uani 1 1 d . . .
O1 O 3.4364(3) 1.00272(16) -1.3002(5) 0.0734(11) Uani 1 1 d . . .
O2 O 3.7448(3) 0.84786(17) -1.3727(4) 0.0698(11) Uani 1 1 d . . .
O3 O 3.7462(3) 0.87722(15) -1.6215(4) 0.0612(9) Uani 1 1 d . . .
O4 O 3.7452(2) 0.98414(15) -1.3233(4) 0.0608(9) Uani 1 1 d . . .
O5 O 3.6464(2) 0.98429(15) -1.1317(4) 0.0620(9) Uani 1 1 d . . .
N1 N 3.4409(3) 0.94631(17) -1.0844(4) 0.0510(10) Uani 1 1 d . . .
H1A H 3.4032 0.9663 -1.0326 0.061 Uiso 1 1 calc R . .
N2 N 3.6365(3) 0.91239(16) -1.4864(4) 0.0473(9) Uani 1 1 d . . .
H2B H 3.6055 0.9229 -1.5726 0.057 Uiso 1 1 calc R . .
N3 N 3.6094(3) 0.93166(16) -1.3466(4) 0.0475(9) Uani 1 1 d . . .
C11 C 3.4877(3) 0.89562(19) -1.0286(5) 0.0453(10) Uani 1 1 d . . .
C12 C 3.4886(4) 0.8715(2) -0.8854(6) 0.0627(14) Uani 1 1 d . . .
H12A H 3.4565 0.8885 -0.8085 0.075 Uiso 1 1 calc R . .
C13 C 3.5396(5) 0.8205(3) -0.8599(7) 0.0768(17) Uani 1 1 d . . .
H13A H 3.5408 0.8026 -0.7641 0.092 Uiso 1 1 calc R . .
C14 C 3.5882(4) 0.7958(2) -0.9713(6) 0.0709(15) Uani 1 1 d . . .
H14A H 3.6210 0.7612 -0.9506 0.085 Uiso 1 1 calc R . .
C15 C 3.5894(4) 0.8216(2) -1.1158(6) 0.0553(12) Uani 1 1 d . . .
H15A H 3.6235 0.8053 -1.1914 0.066 Uiso 1 1 calc R . .
C16 C 3.5385(3) 0.87213(18) -1.1431(5) 0.0421(10) Uani 1 1 d . . .
C17 C 3.5222(3) 0.90948(19) -1.2841(5) 0.0426(10) Uani 1 1 d . . .
C18 C 3.4614(3) 0.9602(2) -1.2267(6) 0.0508(11) Uani 1 1 d . . .
C19 C 3.6671(3) 0.9686(2) -1.2572(6) 0.0502(11) Uani 1 1 d . . .
C20 C 3.8206(4) 1.0203(3) -1.2385(7) 0.0719(16) Uani 1 1 d . . .
C21 C 3.8572(5) 0.9917(4) -1.0874(9) 0.107(2) Uani 1 1 d . . .
H21A H 3.8829 0.9544 -1.1077 0.160 Uiso 1 1 calc R . .
H21B H 3.8047 0.9876 -1.0245 0.160 Uiso 1 1 calc R . .
H21C H 3.9071 1.0151 -1.0340 0.160 Uiso 1 1 calc R . .
C22 C 3.8978(5) 1.0209(4) -1.3476(10) 0.113(3) Uani 1 1 d . . .
H22A H 3.9219 0.9825 -1.3584 0.169 Uiso 1 1 calc R . .
H22B H 3.9498 1.0457 -1.3072 0.169 Uiso 1 1 calc R . .
H22C H 3.8708 1.0350 -1.4467 0.169 Uiso 1 1 calc R . .
C23 C 3.7788(6) 1.0796(3) -1.2156(9) 0.098(2) Uani 1 1 d . . .
H23A H 3.7566 1.0960 -1.3144 0.147 Uiso 1 1 calc R . .
H23B H 3.8279 1.1040 -1.1639 0.147 Uiso 1 1 calc R . .
H23C H 3.7254 1.0765 -1.1542 0.147 Uiso 1 1 calc R . .
C24 C 3.7143(3) 0.8760(2) -1.4827(6) 0.0505(11) Uani 1 1 d . . .
C25 C 3.8305(4) 0.8422(2) -1.6557(7) 0.0669(15) Uani 1 1 d . . .
C26 C 3.9177(4) 0.8579(3) -1.5432(9) 0.095(2) Uani 1 1 d . . .
H26A H 3.9312 0.8983 -1.5517 0.143 Uiso 1 1 calc R . .
H26B H 3.9730 0.8361 -1.5672 0.143 Uiso 1 1 calc R . .
H26C H 3.9042 0.8493 -1.4396 0.143 Uiso 1 1 calc R . .
C27 C 3.8436(6) 0.8607(3) -1.8178(8) 0.104(2) Uani 1 1 d . . .
H27A H 3.7874 0.8501 -1.8856 0.156 Uiso 1 1 calc R . .
H27B H 3.8997 0.8421 -1.8507 0.156 Uiso 1 1 calc R . .
H27C H 3.8520 0.9018 -1.8204 0.156 Uiso 1 1 calc R . .
C28 C 3.8056(5) 0.7790(2) -1.6474(8) 0.0820(18) Uani 1 1 d . . .
H28A H 3.7506 0.7707 -1.7204 0.123 Uiso 1 1 calc R . .
H28B H 3.7905 0.7698 -1.5451 0.123 Uiso 1 1 calc R . .
H28C H 3.8599 0.7563 -1.6716 0.123 Uiso 1 1 calc R . .
C1 C 3.3514(4) 0.8502(4) -1.3462(7) 0.101(3) Uani 1 1 d D . .
C2 C 3.2730(5) 0.8807(5) -1.3223(9) 0.161(6) Uani 1 1 d D . .
H2A H 3.2625 0.9185 -1.3555 0.193 Uiso 1 1 calc R . .
C3 C 3.2000(6) 0.8456(4) -1.2315(8) 0.096(2) Uani 1 1 d D . .
C4 C 3.2214(6) 0.7897(4) -1.1805(9) 0.120(3) Uani 1 1 d D . .
C5 C 3.2979(8) 0.7566(5) -1.2087(13) 0.239(10) Uani 1 1 d D . .
H5A H 3.3103 0.7183 -1.1818 0.287 Uiso 1 1 calc R . .
C6 C 3.3540(8) 0.7946(5) -1.2889(11) 0.170(6) Uani 1 1 d D . .
H6A H 3.4109 0.7765 -1.3101 0.205 Uiso 1 1 calc R . .
C7 C 3.1232(8) 0.8787(5) -1.2101(13) 0.299(14) Uani 1 1 d D . .
H7A H 3.1121 0.9167 -1.2410 0.359 Uiso 1 1 calc R . .
C8 C 3.0639(9) 0.8433(6) -1.1312(15) 0.197(8) Uani 1 1 d D . .
H8A H 3.0050 0.8606 -1.1174 0.237 Uiso 1 1 calc R . .
C9 C 3.0717(6) 0.7885(5) -1.0684(10) 0.141(4) Uani 1 1 d D . .
H9A H 3.0239 0.7741 -1.0116 0.169 Uiso 1 1 calc R . .
C10 C 3.1500(7) 0.7562(6) -1.0912(11) 0.162(5) Uani 1 1 d D . .
H10B H 3.1594 0.7184 -1.0570 0.194 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0523(7) 0.0868(10) 0.0431(7) -0.0056(6) 0.0075(5) -0.0115(6)
O1 0.078(3) 0.063(2) 0.083(3) 0.023(2) 0.023(2) 0.027(2)
O2 0.072(2) 0.079(3) 0.061(2) 0.019(2) 0.0185(18) 0.024(2)
O3 0.067(2) 0.067(2) 0.0544(19) 0.0049(17) 0.0277(17) 0.0134(17)
O4 0.0506(19) 0.067(2) 0.068(2) -0.0075(17) 0.0188(16) -0.0124(17)
O5 0.059(2) 0.066(2) 0.064(2) -0.0174(18) 0.0186(17) -0.0045(17)
N1 0.051(2) 0.052(2) 0.053(2) -0.0029(18) 0.0189(18) 0.0069(18)
N2 0.045(2) 0.057(2) 0.041(2) 0.0016(17) 0.0094(16) 0.0045(18)
N3 0.045(2) 0.053(2) 0.046(2) -0.0028(17) 0.0134(17) -0.0027(17)
C11 0.044(2) 0.047(3) 0.045(2) -0.001(2) 0.0088(19) 0.001(2)
C12 0.071(3) 0.074(4) 0.046(3) 0.001(3) 0.016(2) 0.003(3)
C13 0.097(4) 0.082(4) 0.054(3) 0.023(3) 0.018(3) 0.013(4)
C14 0.085(4) 0.062(3) 0.067(3) 0.018(3) 0.009(3) 0.019(3)
C15 0.062(3) 0.048(3) 0.058(3) 0.002(2) 0.012(2) 0.008(2)
C16 0.042(2) 0.045(2) 0.040(2) -0.0007(19) 0.0077(18) -0.0018(19)
C17 0.039(2) 0.048(2) 0.043(2) 0.0006(19) 0.0092(18) 0.0025(19)
C18 0.045(3) 0.052(3) 0.056(3) 0.004(2) 0.011(2) 0.005(2)
C19 0.048(3) 0.047(3) 0.057(3) -0.001(2) 0.014(2) 0.000(2)
C20 0.052(3) 0.069(4) 0.095(4) -0.006(3) 0.008(3) -0.018(3)
C21 0.073(4) 0.121(6) 0.122(6) 0.013(5) -0.012(4) 0.002(4)
C22 0.066(4) 0.129(7) 0.147(7) -0.011(5) 0.033(4) -0.040(4)
C23 0.106(5) 0.065(4) 0.123(6) -0.014(4) 0.006(5) -0.019(4)
C24 0.050(3) 0.050(3) 0.055(3) -0.001(2) 0.018(2) 0.001(2)
C25 0.060(3) 0.067(3) 0.080(4) -0.009(3) 0.034(3) 0.004(3)
C26 0.056(4) 0.101(5) 0.132(6) -0.030(4) 0.027(4) -0.010(3)
C27 0.119(6) 0.113(6) 0.092(5) 0.003(4) 0.065(5) 0.010(5)
C28 0.080(4) 0.061(4) 0.107(5) -0.012(3) 0.022(4) 0.002(3)
C1 0.067(4) 0.188(8) 0.049(3) -0.027(4) 0.008(3) -0.059(5)
C2 0.048(4) 0.333(16) 0.105(6) -0.106(8) 0.021(4) -0.039(6)
C3 0.097(5) 0.118(6) 0.070(4) -0.022(4) -0.013(4) 0.001(5)
C4 0.087(5) 0.148(8) 0.115(6) -0.045(6) -0.037(5) 0.017(5)
C5 0.34(2) 0.146(11) 0.199(14) -0.063(10) -0.146(15) 0.115(13)
C6 0.175(10) 0.245(14) 0.091(6) 0.019(7) 0.008(6) -0.157(11)
C7 0.36(2) 0.244(17) 0.243(18) -0.166(15) -0.225(18) 0.165(18)
C8 0.166(11) 0.289(19) 0.139(10) 0.005(11) 0.026(8) -0.151(13)
C9 0.107(7) 0.231(12) 0.089(6) 0.002(7) 0.026(5) -0.106(8)
C10 0.085(6) 0.289(16) 0.112(7) 0.007(8) 0.015(5) -0.065(9)
_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.778(6) . ?
S1 C17 1.840(4) . ?
O1 C18 1.206(6) . ?
O2 C24 1.198(6) . ?
O3 C24 1.328(5) . ?
O3 C25 1.481(6) . ?
O4 C19 1.329(5) . ?
O4 C20 1.477(6) . ?
O5 C19 1.213(5) . ?
N1 C18 1.338(6) . ?
N1 C11 1.405(6) . ?
N2 C24 1.369(6) . ?
N2 N3 1.385(5) . ?
N3 C19 1.360(6) . ?
N3 C17 1.470(5) . ?
C11 C12 1.365(7) . ?
C11 C16 1.390(6) . ?
C12 C13 1.384(8) . ?
C13 C14 1.363(8) . ?
C14 C15 1.395(7) . ?
C15 C16 1.376(6) . ?
C16 C17 1.499(6) . ?
C17 C18 1.560(6) . ?
C20 C22 1.504(9) . ?
C20 C21 1.512(9) . ?
C20 C23 1.514(9) . ?
C25 C27 1.503(8) . ?
C25 C28 1.508(8) . ?
C25 C26 1.520(9) . ?
C1 C2 1.333(8) . ?
C1 C6 1.381(9) . ?
C2 C3 1.575(8) . ?
C3 C7 1.342(9) . ?
C3 C4 1.392(8) . ?
C4 C5 1.354(9) . ?
C4 C10 1.533(8) . ?
C5 C6 1.409(9) . ?
C7 C8 1.394(10) . ?
C8 C9 1.383(9) . ?
C9 C10 1.351(9) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C17 98.7(2) . . ?
C24 O3 C25 121.0(4) . . ?
C19 O4 C20 120.3(4) . . ?
C18 N1 C11 112.6(4) . . ?
C24 N2 N3 117.7(4) . . ?
C19 N3 N2 120.5(4) . . ?
C19 N3 C17 117.8(4) . . ?
N2 N3 C17 121.4(4) . . ?
C12 C11 C16 122.4(4) . . ?
C12 C11 N1 128.2(4) . . ?
C16 C11 N1 109.4(4) . . ?
C11 C12 C13 116.9(5) . . ?
C14 C13 C12 121.9(5) . . ?
C13 C14 C15 120.9(5) . . ?
C16 C15 C14 117.9(5) . . ?
C15 C16 C11 120.0(4) . . ?
C15 C16 C17 131.6(4) . . ?
C11 C16 C17 108.4(4) . . ?
N3 C17 C16 116.4(4) . . ?
N3 C17 C18 110.4(4) . . ?
C16 C17 C18 102.4(3) . . ?
N3 C17 S1 106.3(3) . . ?
C16 C17 S1 112.6(3) . . ?
C18 C17 S1 108.6(3) . . ?
O1 C18 N1 127.6(4) . . ?
O1 C18 C17 125.6(4) . . ?
N1 C18 C17 106.8(4) . . ?
O5 C19 O4 126.1(4) . . ?
O5 C19 N3 121.5(4) . . ?
O4 C19 N3 112.4(4) . . ?
O4 C20 C22 101.8(5) . . ?
O4 C20 C21 109.9(5) . . ?
C22 C20 C21 110.8(6) . . ?
O4 C20 C23 108.7(5) . . ?
C22 C20 C23 112.5(6) . . ?
C21 C20 C23 112.5(6) . . ?
O2 C24 O3 128.0(4) . . ?
O2 C24 N2 124.5(4) . . ?
O3 C24 N2 107.5(4) . . ?
O3 C25 C27 102.0(5) . . ?
O3 C25 C28 109.5(4) . . ?
C27 C25 C28 111.9(6) . . ?
O3 C25 C26 109.4(5) . . ?
C27 C25 C26 111.6(6) . . ?
C28 C25 C26 111.9(6) . . ?
C2 C1 C6 115.5(8) . . ?
C2 C1 S1 126.8(7) . . ?
C6 C1 S1 117.7(6) . . ?
C1 C2 C3 112.5(9) . . ?
C7 C3 C4 129.4(9) . . ?
C7 C3 C2 109.7(9) . . ?
C4 C3 C2 120.9(8) . . ?
C5 C4 C3 128.1(9) . . ?
C5 C4 C10 111.4(9) . . ?
C3 C4 C10 120.4(8) . . ?
C4 C5 C6 102.6(10) . . ?
C1 C6 C5 140.2(11) . . ?
C3 C7 C8 104.5(11) . . ?
C9 C8 C7 135.2(12) . . ?
C10 C9 C8 118.8(9) . . ?
C9 C10 C4 111.5(9) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.066